Her Sister?

This is also based on a real event that happened not long before "The Choice You Make".

I rode the bus most of the time in college. I didn't own a car and living in a big city, the easiest way to get around was on the bus. I did most of my homework on the bus and sometimes got into some interesting conversations.

That day, the bus was three quarters full and you could expect that somebody would sit down beside you eventually. So I did not pay any attention when a tall and slender senior lady gets on the bus. She looked around 70, swept back grey hair, probably a knockout in her youth, but nothing to take notice of. She came down the aisle and sat down beside me spreading her legs wide deliberately rubbing her knee up against mine. Now, I was paying attention and she was no lady! Up close, she was a man in drag. But not the type of drag that you see at a poorly lit gay bar.

She dressed tastefully and stylishly appropriate for her age; a broomstick skirt which was fashionable at the time and a frilly blouse with a light jacket overtop. She probably was wearing fake breasts under the blouse, but she did not overdo it, only a B cup. Her makeup was a bit overdone; Lipstick was a touch too red and eyeshadow a touch too blue, but only dowdy rather than slutty. Altogether, I was impressed by the fact that she resisted the common urge among crossdressers to look and behave like a whore. She wanted to look and act like a lady and at first, I was fooled. This lady had her act together.

I could easily rebuff her by simply closing my legs and turning away to look out the window. But I will confess that I knew an openly transwoman at the college and was a bit curious as to whether sex with a transgender person would be more like a man or a woman. But I didn't think I would ever have a real opportunity. Here, this woman was putting the move on me and completely out of the blue. I kept my legs open so that we were rubbing our legs together, not so much that anybody else would notice. If anybody did, they would think we were a young man with his grandmother or kinky grandfather.

I initiated small talk, "Nice day, isn't it?"

She says, "A little warm for me, but I can put up with it." She indicates the book that I am reading, "Are you going to the U?"

"That's right. Just getting caught up on my biology. Might as well, since there is little else to do on the bus."

She looked like she was going to turn away, "Oh, I had better let you do your homework then."

She gave me an out, but in my college years, I would fuck a goat if it would let me. This lady may look like a goat, but an interesting goat; a touch feminine, a touch horny and a lot kinky. I said, "Oh, I don't mind. I was about finished anyway." I turned towards her, pulling my knees together, but also pressing them a little more firmly and fully against hers.

She smiled and looked down at our legs. Her smile said that she recognized an insatiable young man and she started reeling me in, so I let her. A bit of niceties back and forth until my stop was coming up.

She offers, "I bet you haven't had a homecooked meal in a while. Would you like to come over on Sunday and we'll serve you lunch?"

Wait a minute! "We'll?" Who is we!? I say, "I would like that. But who else is going to be there?"

She said, "Just my sister. I want to introduce you."

"My stop is coming up," I warn. "You want to give me your information?' She took my notebook and wrote down her name, "Amanda," a rather pointless and stupid pun, her phone number and an address in a residential neighborhood. Then I had to get off the bus. It was a brief encounter, but filled with potential. I had little doubt that she wanted more from me than to simply clean out her refrigerator. But I was not expecting her to say, that she would introduce me to a sister. Who could she mean? The tamest option is simply referring to herself. My trans friend always referred to her feminine persona in the third person. Maybe that was a coded way of saying that she is dressing as a sister and she has a brotherly persona as well. I had already figured out that she was a transvestite even though she did not say it explicitly and I had not acknowledged it either. This could have been her way to warn off a boy who must have looked like an innocent virgin to her. That does not seem likely, though, because then she would say that she was introducing me to her brother.

The second option was that she had a literal sister who screened all her dates. It would be just good common sense to protect herself; There is safety in numbers. Or... her sister may join us in the bedroom. If having sex with a transvestite was not kinky enough, having sex with a transvestite and her sister would be a unique situation.

A more realistic possibility is that her sister was another transgender roommate. That certainly would have interesting possibilities. I could easily get into two shemales playing with and being played with by me. If it freaked me out, I could run, but not much freaks me out. I assumed that what was underneath her dress was all male parts, but two transgender people living together might support each other in hormone therapy or other interesting transformations. It was a provocative idea.

Perhaps her sister was a wife, girlfriend or dominatrix that insisted on her feminization as a submissive. You read about these situations in erotica, but you also assume that they are all fantasy with no basis in reality. This is going to be my opportunity to find out if there really were women out there who enjoyed making their lovers into sex toys. Amanda may not have been on the bus just to test her performance in public; She might have been on assignment by her dominatrix to bring home a lover. I would not mind playing the bull to a cuckold or a gay dom to a sissy. That has its own potential.

Or perhaps her sister was a succubus who told Amanda was to find innocent virgins to sacrifice on a slate table in a chalk pentagram. Okay! Time to reign it in. My mind was reeling with interesting fantasies, but there was going to be only one way to find out. I would have to keep my date with this old pervert and see what kinky scenario she had set up for a young pervert. I go back to my room and dream about what might happen if I dare.

I dare, but just barely. I should have walked away from this offer, but my curiosity got the best of me. On Sunday, I caught the bus to Amanda's neighborhood. In fact, I got on the bus an hour ahead of what I needed to be certain that I arrived at her house on time. Really, I caught the earlier bus, because I wanted to check out her apartment and see what sort of situation I am getting into before I knocked at the door. Oh, and if she happened to catch me out there a touch early and invited me in for an extra hour of kinky sex, I would not mind. I was both aroused and scared of what I might get myself into. Of course, I had set no time limit. It is not the type of thing that you tell your friends about, so if she tied me up and held me captive in their apartment forever as a sex slave, there would be no one to rescue me.

It was two blocks from the bus stop over to her place. It was one of those cheap bungalows that are divided four or six efficiencies on the inside. They are not uncommon close to my campus and a number of my friends lived in one. They cost about the same as a dorm room without having dorm monitors asking why your room smelled like weed. I have a hard time imagining two mature people living in an apartment that small, but I have known college students to squeeze as many as four people in one, so anything was possible.

I stood across the street and considered crossing the final threshold to becoming this older tranny's sex toy for the afternoon. I could see her moving through the window as she came outside to dump the dustbin into the trash. She looked across the street and saw me standing there and waved me over.

Too late to run now! I waved back and came across the street as if I had just arrived rather than snooping for several minutes. She dressed a bit more seductively than the other day, but only a bit. She truly was a classy lady even when hitting on college students. You might think she was getting ready to go on a social outing. She had switched her blue haired wig for a dark salt and pepper one with a bit more curl and lift to it. She was wearing two inch heels, not provocatively tall; just enough to define her legs and look formal. Her dress was a black satin that clung to the curve of her calves. It was accentuated with large pink lilies that travelled right up to the bottom of her matching jacket and a frilly white blouse underneath. She wore more jewelry; a pearl necklace, clipped on earrings and rings. She looked ready to entertain a gentleman caller. She need not have bothered. I was not that much of a gentleman.

She led me into her house and it was the simple affair that you expect; a very small galley kitchen with a formica dining table for two, a single small bathroom and a bedroom that doubled as a living room. The full-sized bed was made up with a white bedcover with frills around the edges. On a night stand is a lamp with a glass shade with painted flowers. A sturdy loveseat is situated to watch the television. It was all neatly feminine and age appropriate. It might have been my grandmother's house if my grandmother had not lived in a small town and living only on social security. Beside the tv is a selection of movies that are unsurprising to her taste; Titles like "Femboy Delight", "Twinks take the Dick", and "Mandy sucks Candy." I browsed the titles and commented, "Nice."

Amanda looked up as she cut the tenderloin and placed it on two plates. "if you want to put one in, feel free."

I put the videos back down and turned away, not really certain what to do with myself, and not wanting to seem too eager. "Maybe later. So where is your sister?"

Amanda sets the meal down on the table, "Oh, she's coming out later. I hope you aren't in too much of a hurry. I was hoping you could stay all afternoon. You might have a curfew in your dorm, but we don't have any here."

I nervously chuckled, "That's good to know."

We ate our lunch and I ask a bit of her life story, "So how long have you been dressing?"

"Ever since I was your age. Back then, you only did it in burlesque shows or in secret clubs or bars. It was illegal practically everywhere, but word got around as to where you could do it and I did a lot of drag shows. Now, I live fulltime as a woman and nobody seems to mind even if officially it is illegal. How about you, do you dress?"

"No, I don't dress. I am basically straight."

She arched an eyebrow over her wine, "Basically? Well, I won't tell anybody if you don't."

I laughed and suddenly had a need to move. I swallowed the rest of my wine and got up from the table to go into the living/bed room.

She followed. "Don't worry, Dear. I can see this is your first time. We won't go any faster or farther than you want to. Put in one of those movies and come here and sit on the sofa." She patted the loveseat, which hardly counted as a sofa, but her apartment was not much larger than my dorm room, so who was I to quibble? I look at the pornos and select "Mandy Sucks Candy." It sounded like the most straight selection. It wasn't. Mandy, as I guessed, turned out to be a shemale, so was Candy. But I still sit down next to Amanda and she puts her arm around my shoulders turning towards me. She asked, "Are you a virgin?"

"No, I have a girlfriend, back in my hometown."

"But none here? How many times have you done it?"

"Oh, a few times," I said, but she seemed a bit disappointed, so I admitted the truth, "Just on our prom night. We made out and she gave me a blowjob."

She placed a long slender leg over mine, trapping me in place. The move is very provocative and I started to get hard with my big cock needing release from suddenly very tight jeans. She leaned in and ran one of a long fingernail down my neck and said softly, "So...I am going to be your first transvestite?"

"I guess."

She pouted coquettishly, "You guess? You aren't certain if it is your first time with a transvestite or not?"

"No. I mean. You will be my first."

"Oh! Good! I like breaking in a virgin! Don't you worry. I don't have to go home to Mommy after giving you a blowjob either. I will teach you a few tricks that your girlfriend hasn't even imagined yet." She glanced at the tv and says, "Oh! This is a good part! Mandy and Candy are going to 69 and together they must have 19 inches down each other's throats." I stare fascinated as the transgender porn stars swallow each other up, while Amanda ignored the video and started nibbling on my neck. I was a bit nervous and stiff, but she was putting me at ease. I enjoyed the feeling of her lips and tongue kissing my skin and causing tingles to run down to my stomach. I couldn't help but get hard. Of course, I was always hard. I felt I should reciprocate somehow, so I put my arm around her slender body and pulled her closer until she was almost sitting on my lap as she sucked on the nape of my neck. She asked quietly, "Isn't that hot, seeing two sexy women with big cocks sucking each other off?"

I looked back at the screen. They are tall and buxom and I could imagine cupping their generous breasts, undoubtedly enhanced by silicone. "Yeah! I would love to see two drag queens go at it like that."

Amanda asked, "Do you ever dress like a woman?"

"Me? No never!"

"But you have a pair of your girlfriend's underwear in your drawer."

How could you possibly know that?! I protest, "That's different. She gave that as a momento before I left for college." I kept it hidden in the bottom drawer of my dresser and smell her perfume and a bit of the lingering scent of her juices. Truth was that the scent of her was almost gone, but I still stroked the silky fabric up and down my cock when I masturbated.

And Amanda placed her fingers on my lips, "Shh! Shh! I know. I know. I stole my first pair from my sister. It's okay. I used to slide it up and down on my cock. It felt so smooth and silky. I just had to try it on, but my sister's was too small, so I stole a pair from a friend. I pulled it on over my ass and from then on, I was hooked. I collected more and more women's clothing until now, it is all I own. I never dress like a man anymore. Not once in the last ten years. It is so liberating when you can just be yourself and not worry about what anybody else thinks. Would you like to try it?"

"I don't know. I have never really thought about it..."

"But you want to try it. Don't you? Come on. Just for the afternoon and then you can be Candy and I'll be Mandy and we'll suck each other just like in the video."

I looked at the two shemales going to town on each other. Why the fuck not? It was just the two of us and there is a code of honor between lovers. At least, there ought to be a code of silence between lovers. "Okay. I'll try it just once."

"I knew you would," she said practically jumping off of my lap. "Take your clothes off." She walked over to her dresser and her ass swayed in a manner that girls my age almost never let happen, but I liked it. She opened up the second drawer where she has some preselected items ready to go. A bit too ready to go, but if she hadn't been prepared, I might have chickened out. I probably should have ran out the door and back to the the bus stop. But this would have insulted her and she had been nice enough so far. If anything sweetly nice, and this sounded like too much fun. She had not suggested to do anything which did not fit with a few secret fantasies of mine; to have sex with a woman that also had the lust of a man, to take on the persona of a woman myself, even to get on my knees and suck cock. This was all provocatively exciting. The tingle in my stomach was a combination of fear and arousal and I decided to follow the arousal.

I looked at this woman. You hear about cougars, May-December relationships and there was a huge age gap between us. She was more like my grandmother than a friend, but that was interesting in of itself. She seemed so confident and mature. She would not judge me for my dirty thoughts and feelings. She probably has tried all of my kinkiest fantasies and could teach me a few that I had never thought of before. I could be accepted and even encouraged to explore those half-formed ideas that made me keep a pair of my girlfriend's dirty unwashed underwear hidden in my drawer.

I took off my t-shirt. I was a scrawny teenage boy. My chest was flat and hairless with small pink nipples and rib bones sticking out. Nobody accused me of looking manly. Back then, homosexuals called young men like me "Twinks." Amanda turned and purred, "Oh, Aren't you, Darling?! I bet you have more girlfriends than you know what to do with!"

I blushed at the compliment and admitted, "No. Not really. I am not much of a ladies' man."

She stepped closer and cupping the back of my head with her long slender fingers gave me a gentle, but firm kiss on the mouth. Her kiss was slow and passionate running her tongue over my lips, before she pulled away and said, "No need to be shy. If you weren't a ladies' man before, you'll be a man's lady before you leave."

I countered, "I don't think I will make a very good drag queen."

She smiled and winked a long eyelash at me, "That's something else we'll keep between us, Sisters." Her hands reached down and unsnapped my jeans, running around the waistline to cup my boyish ass and pull me against her, while allowing the jeans and underwear to slip off me to the floor. She looked down at my seven inches rubbing against her skirt and said, "Ummm! Nice! You are well hung."

I was a bit surprised and look down, "You think so? I don't think I am that big. Mandy and Candy are certainly bigger."

She laughed, "Those are porn stars, Honey. That's not real life. You got nothing to be ashamed of in that department, but let's see what you look like as my sister. I am curious and I bet you are, too."

It finally dawned on me what she had been saying, "Oh! You meant that you were going to make me your sister?!"

Amanda laughed with a big smile, "Now, you're getting it! I knew the instant that I saw you reading on the bus that you would make a cute little sorority sister, even if you did not know it yourself. It was just a matter of introducing you to her. How about it, stud? Are you willing to try something new or are you too manly for that?"

I was too manly for that, but my cock was telling me to try it and swelling with a hot sexy tingle. Amanda looked down at the cock as it swelled and twitched with her hands across her chest knowingly. I could not deny the visible evidence that the idea was intriguing me, "Okay, as long as we keep it between us....Us, Sisters."

Amanda agreed, "Just us, Sisters." She finished pulling out appropriate clothing for our escapade. She was taller than me, but similar in build so that most of what she had probably came from her own boudoir without needing anything special or different.

I stood before her naked; a scrawny assed horny teenage college student and she worked with practiced ease and soft touch like my own grandmother dressing me for church as a toddler, but instead of an Easter suit, I was being placed in an Easter dress, literally. She did not hold back her selections for my first time. She started her layering with some latex prosthetics that gave me perky young breasts and cupped them in a soft silky bra like you cannot buy anymore at department stores. She tried to tuck my cock into a matching set of panties, but I was turned on by her rubbing against me and playing with my body, so she left the tip rising above the feminine illusion and said, "Don't worry after it cums and relaxes. It will slide into place for a picture between us sisters."